13444-10-5

Usage

General Description

5H-Tetrazol-5-one, 1,4-dihydro-1-phenyl-4-(2-propenyl)- is a chemical compound that belongs to the class of tetrazoles. It is also known by the name "Flibanserin." Flibanserin is a drug that has been approved by the FDA for the treatment of hypoactive sexual desire disorder (HSDD) in women. It works by affecting serotonin and dopamine levels in the brain, leading to an increase in sexual desire. Flibanserin is also being studied for its potential use in other conditions, such as depression and anxiety. However, it has also been associated with side effects such as dizziness, fatigue, and low blood pressure, and its use comes with strict safety warnings and restrictions.

Upstream product

• 13437-77-9 1-phenyl-5-(prop-2-enyloxy)-tetrazole 
• 14210-25-4 5-Chloro-1-phenyltetrazole 
• 5097-82-5 5-phenyl-1H-tetrazolone 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 866639-44-3 3,4-dihydro-3-phenylpyrimidin-2(1H)-one 
• 103-71-9 phenyl isocyanate 
• 62-53-3 aniline 
• 95926-75-3 (E)-1,3-Dihydro-1-(1-propenyl)-2H-benzimidazol-2-on 
• 72798-66-4 1,3-Dihydro-1-(2-propenyl)-2H-benzimidazol-2-on 

Relevant academic research and scientific papers

Mechanistic investigations into the photochemistry of 4-allyl-tetrazolones in solution: A new approach to the synthesis of 3,4-dihydro-pyrimidinones

Photolysis (λ = 254 nm) of 4-allyl-tetrazolones 2a-c was carried out in methanol, 1 -propanol, 1-hexanol, acetonitrile, and cyclohexane. The sole primary photochemical process identified was molecular nitrogen elimination, with formation of pyrimidinones 6a-c. Following the primary photocleavage, secondary reactions were observed in acetonitrile and cyclohexane, leading to phenyl-isocyanate (7), aniline (9), and 1-phenylprop-1-enyl-isocyanate (10a). In alcoholic solutions, the primary products, 6a-c, remained photostable even under extended irradiation, making possible the isolation of 3,4-dihydro-pyrimidinones as stable compounds in very high yields. The observed photostability of pyrimidinones 6a-c in alcohols is ascribed to the excited state quenching via reversible proton transfer, facilitated by the solvent cage stabilization due to formation of hydrogen bonds. The viscosity of alcohols is directly related to the cage effects observed. The photocleavage of 4-allyl-tetrazolones leads probably to a caged triplet radical pair. This hypothesis is confirmed by the solvent viscosity effect on the photolysis quantum yields. Additionally, dissolved molecular oxygen sensitizes the formation of pyrimidinones, as should be expected for a triplet intermediate that can only form the product molecule after T-S conversion, which is accelerated by oxygen.

Novel efficient synthesis of 3,4-dihydro-6-substituted-3-phenylpyrimidin- 2(1H)-ones

A new attractive and convenient strategy for the synthesis of 3,4-dihydro-6-substituted-3-phenylpyrimidin-2(1H)-ones is described. Photolysis (λ = 254 nm) of 4-allyl-tetrazolones in alcoholic solutions produces the corresponding pyrimidinones as the sole product in nearly quantitative yields, with simultaneous extrusion of molecular nitrogen. Work-up procedures consist in the simple evaporation of the solvent under reduced pressure, in mild conditions. Heats of reaction for the photocleavage process of 4-allyltetrazolones were calculated, indicating high stability of the resulting products.

A kinetic investigation of the thermal rearrangement of allyloxytetrazoles to N-allyltetrazolones

The mechanism of the thermal rearrangement of 1-aryl-5-allyloxytetrazoles 1 to give 1-aryl-4-allyltetrazolones 2 in very high yield has been investigated through kinetic studies in one polar and one less polar solvent. The results suggest mainly a concerted [3,3] sigmatropic process, in which a partially positively charged allyl group migrates from oxygen to nitrogen, similar to the polar transition state found in the Claisen rearrangement.

Metal-assisted reactions. Part 25. Heterogeneous and homogeneous catalytic transfer hydrogenolysis of allyloxytetrazoles to yield alkenes or alkanes

Transfer hydrogenolysis of 5-allyloxy-1-phenyltetrazoles using either a heterogeneous or a homogeneous palladium catalyst and a hydrogen donor leads to cleavage of the allyloxy C-O bond to yield an alkane or an alkene and 1-phenyltetrazolone, depending on the catalyst used.

Photoextrusion of Nitrogen from 1,4-Dihydro-1-phenyl-5H-tetrazol-5-ones and -thiones. Benzimidazolones and Carbodiimides

Alkylation of 1-phenyltetrazolone 10a with 2-cyclohexen-1-yl bromide followed by dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone permits introduction of a phenyl group at N-4 of the tetrazole ring via the sequence 10a -> 10f -> 10g.The photoextrusion of molecular nitrogen from the (N-4)-substituted 1-phenyltetrazolones, 10a (hydrogen), 10b (methyl), 10d,e (propenyl), and 10g (phenyl) produces essentially quantitative yields of the corresponding benzimidazolones 14a,b,d,e,g.On irradiation of the 1-phenyltetrazolethiones 8b,f,g the carbodiimides 22b,f,g are obtained together with molecular nitrogen and sulfur, while 8a affords phenylcyanamide (25).In contrast to the thermolysis, which is known to give 2-(methylamino)benzothiazole (21b), photolysis of the (phenylimino)-1,2,3,4-thiatriazole 24, an isomer of methylphenyltetrazolethione 8b, also yields molecular nitrogen, sulfur, and methylphenylcarbodiimide (22b).